Senior Software Engineer - Real Estate Technology

Why Aiola CPA, PLLC

• Specialized Focus – We work exclusively with real estate investors. You'll be solving real problems for a specific audience, and you'll get very good at it.
• Fully Remote – We've been fully virtual from day one. Work from wherever you do your best work.
• Autonomy – You'll have ownership over what you build and how you build it. We set clear goals and trust you to get there.
• Growth Opportunity – This is a ground-floor role on our technology side. We're investing heavily in AI and internal software, and this role has a direct path into firm leadership.
• People-First Culture – Unlimited PTO, flexible scheduling, hobby days, and team trips and trainings. We genuinely value the people on this team.

Role Overview

Aiola CPA is a virtual CPA firm serving real estate investors across the US. Our goal is to be a leader in our niche. AI is changing the landscape of professional services, and we want to make sure we are out in front of it as leaders in the space.

This role is about helping us build for what comes next. You will design and maintain the internal software apps and AI systems that make us better, more efficient, and more valuable to our clients. That includes replacing an expensive SaaS tech stack with customized tools we actually build for our specific purposes. But the bigger opportunity is using AI to push the firm forward and redefine what advisory, tax, and accounting services look like entirely.

One non-negotiable for us is the importance of security. We handle sensitive data like SSNs, financial records, and tax filings for hundreds of clients. Every system or tool you build needs to meet industry security standards – encryption in transit and at rest, proper access controls, secure authentication, real monitoring, and adherence to Section 7216. This is the foundation from which we build.

Outcomes

Here is what we expect this role to deliver.

• Audit and replace – at least 3 high-cost SaaS tools within the first 12 months with custom-built alternatives that match or improve on what we have today
• Cut SaaS spend – by at least $40,000 within the first 12 months
• Build and deploy – a minimum of 5 AI-powered tools or automations within the first 6 months that reduce manual work across the firm
• Keep things running – 99%+ uptime on all production tools you build, with incidents documented and resolved within 24 hours
• Document everything – All code lives in the shared repo. All systems have written documentation. Nothing critical exists only in your head.
• Deliver a quarterly roadmap – showing what has been completed, what is in progress, and what is planned across all technology priorities.

Attributes

These are the qualities we look for. Not credentials, just how you work.

• Ownership – You build it, you own it. You see things through and take responsibility when something goes sideways.
• Technical Depth – You write real, maintainable code and you understand it at every level. You can debug your own work without needing someone else to step in.
• Resourcefulness – When you hit a wall, you find a way through. You do not wait to be unblocked.
• Business Curiosity – You want to understand how the firm works, not just the technical requirements. The best tools come from people who understand the problem well.
• Communication – You keep people informed. Status updates, blockers, changes in direction – the team always knows where things stand.
• Security Mindset – You think about how data could be exposed or mishandled before anyone asks you to. Client trust is something you take personally.

Non-Negotiables

• Write real code – You understand what you are shipping. If you cannot explain it, it does not go to production.
• Own what you build – When something breaks, you fix it. We value people with agency who can find solutions to problems they encounter.
• Document as you go – Every system in the shared repo, fully documented. Future teammates should be able to pick up your work without a phone call.
• Protect client data – Our clients share sensitive financial information with us. Every tool you build reflects that responsibility.
• Communicate consistently – As a virtual firm, it’s vital for you to provide consistent updates and ask proactive questions. Keep the team in the loop and you’ll avoid issues before they even surface.

Technical Requirements

This is the first hire of this nature at the firm. We do not have a fully built-out training program for the specific role and responsibilities themselves, but we will provide thorough training on the software and systems we currently use. We expect you to hit the ground running from a technical standpoint.

Core Engineering

• Backend – Python and/or Node.js at a production level
• Frontend – React or equivalent – you can build functional, clean interfaces
• Databases – Solid SQL fundamentals, data modeling, and working knowledge of NoSQL
• APIs – REST, webhooks, OAuth – you have integrated with third-party services before and know how they work
• Version control – Git, used properly – organized commits, clean history, reviewable code

AI & Automation

• LLM integration – You have built real things with the OpenAI or Claude API, not just exploratory demos
• Agent frameworks – Familiarity with LangChain, AutoGen, or similar tools
• Workflow automation – You have connected AI to real business processes in a way that people actually use

Security & Deployment

• Encryption – You implement encryption in transit and at rest as a default, not an afterthought
• Access controls – Role-based permissions, MFA, OAuth, and least-privilege access are standard practice for you
• Compliance awareness – Some familiarity with SOC 2 concepts, data retention requirements, and audit logging in a regulated environment
• Hosting & deployment – You have shipped and maintained web apps in a real cloud or VPS environment
• Monitoring – You set up logging and alerting proactively so you know about problems before the rest of the team does

Industry-Specific Requirements

We operate in a regulated industry, and that shapes how we build. IRC §7216 governs the use and disclosure of client tax return information, and that includes how AI tools interact with that data. You do not need to know this going in – we will walk you through it. What matters is that you are someone who learns the rules of the environment you are working in and applies them when building. We will provide the compliance context and expect you to build around it.

Metrics of Success

How we will know this is working.

• Weekly (Leading): Project status update delivered by Friday EOD – Every week
• Weekly (Leading): Open incidents or system issues resolved – Within 24 hours
• Monthly (Leading): Active builds and milestones reported – By the 3rd business day of each month
• Quarterly (Lagging): SaaS tools replaced with internal builds – Minimum 1 per quarter in Year 1
• 12-Month (Lagging): SaaS cost reduction – $40,000 or more
• Ongoing (Leading): Production systems documented in shared repo – 100%
• Ongoing (Leading): Security standards applied to all deployed tools – Zero exceptions

Growth Path

We are hiring with the long term in mind. For the right person, here is where this goes:

• Technology Manager – You own the full roadmap and lead additional engineering resources as the team grows
• Director of Technology – You set the technology strategy for the firm and oversee how AI is integrated across every service line
• Chief Technology Officer – You define and execute our technology vision, strategy, and R&D efforts – the person driving the innovation agenda that keeps Aiola CPA ahead of the curve

We are building toward this path with intention. The right person will grow into it.

Application Process

1. Apply. Send your resume and a brief note about the most interesting internal tool or automation you have built. You can include it in your message or email nick@aiolacpa.com directly. Applications without a note will not be considered.

2. Quick Chat. 15 minutes with our Director of Operations.

3. Attribute and Aptitude Tests. A few short online assessments, about 10 minutes each.

4. Team Interview. A conversation with our CEO, Director of Operations, and Senior Tax Advisor.

5. Case Study. A practical exercise to see how you think and how you build.

6. 1-on-1 Interview. A follow-up conversation with our CEO.

7. Offer. If it's a fit, we move quickly.

If this sounds like the right opportunity for you, we would love to hear from you.

(We respect your privacy – everything stays confidential.)